My situation is a little different,
My trail jeep is not registered so street driving is not an issue. In the begining of the season, I perform my routine maitenance, oil change, grease this and that, fluid checks, check wear items. I usually spend a good day just going through everything. after that, I simply repair what I determine from operation needs to be addressed. worse case sinerio, if the YJ isn't wheelable, I bring the 2A, which is registered and is a street mainly jeep, so most maitenance is taken care of through regular driving and tuning.
Honeslty, I stop carrying a lot of extra stuff, I do not carry diff fluid anymore or AFT or engine fluid. I do carry brake fluid and Power steering fluid though; those are what I ID as fluids I can not save if trail fix is needed. I carry spare yoke with joint and straps, belt, and a couple small coils of wire. I leave at the trailer spare shafts, spare tire, and a lot of larger hard parts tat I keep in the tool box.